3-Bromo-5-(trifluoromethyl)benzoic acid → 3-Bromo-N-[4-(4-fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide

HRID 878362Notes

Reaction equation

HRID 878362 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10][C:9]=2[NH:15][CH3:16])=[C:4]([O:17][CH3:18])[CH:3]=1.[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23]([OH:25])=O>>[Br:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23]([N:15]([C:9]1[CH:10]=[N:11][C:12]([CH3:14])=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[O:17][CH3:18])[CH3:16])=[O:25]

Participants

3

Reactant 2

HCID 110867883-Bromo-5-(trifluoromethyl)benzoic acidHCID 706636684-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine

Product 1

HCID 706632723-Bromo-N-[4-(4-fluoro-2-methoxy-phenyl)-6-methyl-pyridin-3-yl]-N-methyl-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from 4-(4-fluoro-2-methoxyphenyl)-N,6-dimethylpyridin-3-amine and 3-bromo-5-(trifluoromethyl)benzoic acid after a reaction time of 20 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless solid (88%). MS (ESI): m/z=497.05 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-5485690cf1a349bfbbfe84b944bf1ddd
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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